NP-MRD: Showing NP-Card for Chuangxinmycin (NP0021091)

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Record Information

Version

2.0

Created at

2021-01-06 06:23:06 UTC

Updated at

2021-07-15 17:35:26 UTC

NP-MRD ID

NP0021091

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chuangxinmycin

Provided By

NPAtlas

Description

Chuangxinmycin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Chuangxinmycin is found in Actinoplanes tsinanensis. Chuangxinmycin was first documented in 1977 (PMID: 327539). Based on a literature review a small amount of articles have been published on Chuangxinmycin (PMID: 11558613) (PMID: 12372526) (PMID: 2800539).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120403D          

 27 29  0  0  0  0            999 V2000
    2.2616    1.5983    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768    0.7088    0.7405 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0459    0.9291    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652    2.1056   -0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259    1.8928   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    0.6120   -0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2779   -0.1847   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699   -1.5335   -0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553   -2.0960    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601   -1.2837    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0543    0.0175    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4405   -1.9081    1.1510 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7371   -0.6977    0.7978 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4323   -1.1787   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639   -0.3979   -1.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488   -2.4521   -0.5498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2438    2.6163    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620    1.8158   -1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014    1.2270    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575    1.1052    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0727    3.0751   -0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4847    2.5874   -1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    0.2631   -1.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1784   -2.0933   -0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860   -3.1341    0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681   -0.8030    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6160   -2.7913    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  2  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  1  0  0  0
  4 21  1  0  0  0  0
  5 22  1  0  0  0  0
  7 23  1  0  0  0  0
  8 24  1  0  0  0  0
  9 25  1  0  0  0  0
 13 26  1  1  0  0  0
 16 27  1  0  0  0  0
M  END


  Mrv1652306242120403D          

 27 29  0  0  0  0            999 V2000
    2.2616    1.5983    0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768    0.7088    0.7405 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0459    0.9291    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652    2.1056   -0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259    1.8928   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    0.6120   -0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2779   -0.1847   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2699   -1.5335   -0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553   -2.0960    0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601   -1.2837    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0543    0.0175    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4405   -1.9081    1.1510 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7371   -0.6977    0.7978 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4323   -1.1787   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5639   -0.3979   -1.3822 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488   -2.4521   -0.5498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2438    2.6163    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620    1.8158   -1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3014    1.2270    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2575    1.1052    1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0727    3.0751   -0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4847    2.5874   -1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1625    0.2631   -1.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1784   -2.0933   -0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1860   -3.1341    0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681   -0.8030    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6160   -2.7913    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  2  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  1  0  0  0
  4 21  1  0  0  0  0
  5 22  1  0  0  0  0
  7 23  1  0  0  0  0
  8 24  1  0  0  0  0
  9 25  1  0  0  0  0
 13 26  1  1  0  0  0
 16 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021091

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1([H])SC2=C([H])C([H])=C([H])C3=C2C(=C([H])N3[H])[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H11NO2S/c1-6-7-5-13-8-3-2-4-9(10(7)8)16-11(6)12(14)15/h2-6,11,13H,1H3,(H,14,15)/t6-,11+/m0/s1

> <INCHI_KEY>
DKHFLDXCKWDVMF-UPONEAKYSA-N

> <FORMULA>
C12H11NO2S

> <MOLECULAR_WEIGHT>
233.29

> <EXACT_MASS>
233.051049772

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.775935667673743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R)-5-methyl-7-thia-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,8,10-tetraene-6-carboxylic acid

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.483691983

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.96907945882112

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.208763173852701

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
63.66210000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R)-5-methyl-7-thia-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,8,10-tetraene-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       2.262   1.598   0.017  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.277   0.709   0.741  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.046   0.929   0.176  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.565   2.106  -0.350  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.826   1.893  -0.768  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.171   0.612  -0.540  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.278  -0.185  -0.735  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.270  -1.534  -0.354  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.155  -2.096   0.226  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.060  -1.284   0.412  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.054   0.018   0.049  0.00  0.00           C+0
HETATM   12  S   UNK     0       0.441  -1.908   1.151  0.00  0.00           S+0
HETATM   13  C   UNK     0       1.737  -0.698   0.798  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.432  -1.179  -0.418  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.564  -0.398  -1.382  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.949  -2.452  -0.550  0.00  0.00           O+0
HETATM   17  H   UNK     0       2.244   2.616   0.509  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.962   1.816  -1.028  0.00  0.00           H+0
HETATM   19  H   UNK     0       3.301   1.227   0.117  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.258   1.105   1.803  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.073   3.075  -0.435  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.485   2.587  -1.213  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.162   0.263  -1.196  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.178  -2.093  -0.541  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.186  -3.134   0.505  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.468  -0.803   1.636  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.616  -2.791   0.160  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    1    3   13   20                                             
CONECT    3    2    4   11                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   22                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    3    6                                                  
CONECT   12   10   13                                                       
CONECT   13   12   14    2   26                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   27                                                       
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    2                                                            
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26   13                                                            
CONECT   27   16                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-(4S,5R)-Chuangxinmycin	ChEBI
(4S,5R)-(-)-Chuangxinmycin	ChEBI
Chuanghsinmycin	ChEBI
cis-(-)-3,5-Dihydro-3-methyl-2H-thiopyrano(4,3,2-CD)indole-2-carboxylic acid	ChEBI
cis-(-)-3,5-Dihydro-3-methyl-2H-thiopyrano(4,3,2-CD)indole-2-carboxylate	Generator
Chuangxinmycin	ChEBI

Chemical Formula

C₁₂H₁₁NO₂S

Average Mass

233.2900 Da

Monoisotopic Mass

233.05105 Da

IUPAC Name

(5S,6R)-5-methyl-7-thia-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,8,10-tetraene-6-carboxylic acid

Traditional Name

(5S,6R)-5-methyl-7-thia-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,8,10-tetraene-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](SC2=C3C(NC=C13)=CC=C2)C(O)=O

InChI Identifier

InChI=1S/C12H11NO2S/c1-6-7-5-13-8-3-2-4-9(10(7)8)16-11(6)12(14)15/h2-6,11,13H,1H3,(H,14,15)/t6-,11+/m0/s1

InChI Key

DKHFLDXCKWDVMF-UPONEAKYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actinoplanes tsinanensis	NPAtlas	327539

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.34	ALOGPS
logP	2.48	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	63.66 m³·mol⁻¹	ChemAxon
Polarizability	23.78 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA028492

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2301053

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3037261

PDB ID

Not Available

ChEBI ID

79391

Good Scents ID

Not Available

References

General References

Authors unspecified: Studies on a new antibiotic--Chuangxinmycin. Sci Sin. 1977 Jan-Feb;20(1):106-12. [PubMed:327539 ]
Yoshida T, Ito A, Ibusuki K, Murase M, Kotani E: Improved preparation of sulfur substituted 3-vinylpyrrole and its application to the syntheses of chuangxinmycin derivatives. Chem Pharm Bull (Tokyo). 2001 Sep;49(9):1198-202. doi: 10.1248/cpb.49.1198. [PubMed:11558613 ]
Brown MJ, Carter PS, Fenwick AS, Fosberry AP, Hamprecht DW, Hibbs MJ, Jarvest RL, Mensah L, Milner PH, O'Hanlon PJ, Pope AJ, Richardson CM, West A, Witty DR: The antimicrobial natural product chuangxinmycin and some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase. Bioorg Med Chem Lett. 2002 Nov 4;12(21):3171-4. doi: 10.1016/s0960-894x(02)00604-2. [PubMed:12372526 ]
Cao J, Qi TQ: [A study on indolepyruvic acid methyltransferase in chuangxinmycin-producing strain]. Wei Sheng Wu Xue Bao. 1989 Feb;29(1):63-7. [PubMed:2800539 ]

Showing NP-Card for Chuangxinmycin (NP0021091)

MOL for NP0021091 (Chuangxinmycin)

3D MOL for NP0021091 (Chuangxinmycin)

3D SDF for NP0021091 (Chuangxinmycin)

3D-SDF for NP0021091 (Chuangxinmycin)

PDB for NP0021091 (Chuangxinmycin)

3D PDB for NP0021091 (Chuangxinmycin)

SMILES for NP0021091 (Chuangxinmycin)

INCHI for NP0021091 (Chuangxinmycin)

Structure for NP0021091 (Chuangxinmycin)

3D Structure for NP0021091 (Chuangxinmycin)